Composition comprising a monomeric compound with an optical effect, process using said composition, monomeric compound, polymer comprising the same and use thereof
Abstract
The invention relates to a cosmetic or pharmaceutical composition containing, in a physiologically-acceptable medium, at least one polymer comprising at least one novel monomeric compound having optical effect properties. The invention also relates to a cosmetic method of making up or caring for keratin materials, such as the skin belonging to the body or face, lips, nails, eyelashes, eyebrows and/or hair, consisting in applying one such cosmetic composition to said materials. The invention further relates to novel monomeric compounds having formula (I) and optical properties, the polymers comprising same and the uses thereof in a composition in order to provide said composition with optical effects, e.g. fluorescence or optical brightening.
Claims
exact text as granted — not AI-modified1 . A cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one polymer comprising at least one monomeric compound of formula (I):
in which:
R1 represents a linear, branched and/or cyclic, saturated and/or unsaturated carbon-based radical containing 1 to 32 carbon atoms; optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
R 2 and R 3 , which are present on the same ring or each on a different ring, represent, independently of each other, a hydrogen, a halogen or a group of formula —X-G-P (II), with the proviso that at least one of the radicals R 2 and/or R 3 represents a group of formula (II), in which:
X is chosen from the groups —O—, —S—, —SO—, —SO 2 —, —NH— and —NR 4 — with R 4 representing a linear, branched and/or cyclic, saturated and/or unsaturated carbon-based radical containing 1 to 30 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
G is a linear, branched and/or cyclic, saturated and/or unsaturated divalent carbon-based radical containing 1 to 32 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
P is a polymerizable group chosen from one of the following formulae:
in which:
R′ represents H or a linear or branched, saturated C 1-6 hydrocarbon-based radical,
X′ represents O, NH or NR″ with R″ representing a radical chosen from C 1-6 alkyl, C 6-10 aryl, (C 6-10 )-aryl(C 1-6 )alkyl and (C 1-6 )alkyl(C 6-10 )aryl radicals, the alkyl and/or aryl groups also possibly being substituted with one or more groups chosen from OH, halogen, C 1-6 alkoxy and C 6-10 aryloxy;
and
m is equal to 0 or 1; n is equal to 0 or 1 and p is equal to 0, 1 or 2.
2 . The composition as claimed in claim 1 , in which, in the monomeric compound, R1 is a cyclic, linear and/or branched, saturated or unsaturated hydrocarbon-based radical, optionally comprising a hydrocarbon-based ring which is itself saturated or unsaturated, containing 3 to 18 and especially 4 to 14 carbon atoms, and may comprise at least one heteroatom, especially one or two nitrogen, oxygen or silicon atoms.
3 . The composition as claimed in either of the preceding claims, in which, in the monomeric compound, R1 is a linear, branched and/or cyclic, saturated or unsaturated hydrocarbon-based radical containing 6 to 13 carbon atoms.
4 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, R1 is chosen from n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, cyclooctyl, decyl, cyclodecyl, dodecyl, cyclododecyl, p-tert-butylcyclohexyl, benzyl and phenyl radicals or a radical chosen from ethyl-2-N-pyrrolidine, (2-methyl)-1-ethylpyrrolidine, 3-propyl-triethoxysilane, dialkylpyrimidines and especially 2-(4,6-dimethyl)pyrimidine, the benzothiazyl radical and the fluorenyl radical.
5 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, the radical R 2 is a hydrogen atom and R 3 is a group of formula (II).
6 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, in the group of formula (II), X is chosen from —O—, —S—, —NH— and —NR 4 —.
7 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, the radical R 4 represents a linear, branched and/or cyclic, saturated or unsaturated hydrocarbon-based radical optionally comprising a hydrocarbon-based ring that is itself saturated or unsaturated, containing 2 to 18 and especially 3 to 12 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S; especially an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, octyl, decyl, dodecyl, phenyl or benzyl radical.
8 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, the divalent radical G is a linear, branched and/or cyclic, saturated or unsaturated divalent hydrocarbon-based radical optionally comprising a hydrocarbon-based ring that is itself saturated or unsaturated, containing in total 2 to 18 and especially 3 to 10 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P and Si.
9 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, G is chosen from linear or branched, saturated divalent hydrocarbon-based radicals optionally comprising a saturated hydrocarbon-based ring, containing in total 2 to 18 and especially 3 to 10 carbon atoms.
10 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, G is chosen from ethylene, n-propylene, isopropylene (or 1-methylethylene and 2-methylethylene), n-butylene, isobutylene, pentylene, especially n-pentylene, hexylene, especially n-hexylene, heptylene, cyclohexylene, octylene, decylene, cyclohexyl-dimethylene especially of formula —CH 2 —C 6 H 10 —CH 2 —, and dodecylene radicals.
11 . The composition as claimed in one of the preceding claims, in which, in the monomeric compound, the polymerizable group P is chosen from one of the following formulae:
in which R′ represents H or methyl.
12 . The composition as claimed in one of the preceding claims, in which the monomeric compound corresponds to one of the following formulae:
13 . The composition as claimed in one of the preceding claims, in which the polymer is a homopolymer of a monomeric compound as defined in one of claims 1 to 12 .
14 . The composition as claimed in one of claims 1 to 12 , in which the polymer is a copolymer comprising only monomeric compounds as defined in one of claims 1 to 12 .
15 . The composition as claimed in one of claims 1 to 12 , in which the polymer is a copolymer comprising at least one monomeric compound as defined in one of claims 1 to 12 , and at least one additional comonomer.
16 . The composition as claimed in either of claims 14 and 15 , in which the polymer is a statistical, alternating, grafted, block or gradient copolymer.
17 . The composition as claimed in either of claims 15 and 16 , in which the monomeric compound is present in an amount of from 0.01% to 70% by weight relative to the weight of said polymer, especially in an amount of from 0.1% to 50% by weight, in particular from 0.5% to 30% by weight, or even from 1% to 20% by weight and better still from 2% to 10% by weight, the additional comonomers, alone or as a mixture, representing the remainder to 100% by weight.
18 . The composition as claimed in one of claims 15 to 17 , in which the polymer comprises at least one additional comonomer chosen, alone or as a mixture, from the following monomers:
(i) ethylenic hydrocarbons containing from 2 to 10 carbons, such as ethylene, isoprene or butadiene; (ii) the (meth)acrylates of formula: CH 2 ═CHCOOR 3 or in which R 3 represents: a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si (R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; R 3 may especially be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyclohexyl, t-butyl-cyclohexyl or stearyl group; 2-ethylperfluorohexyl; or a C 1-4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl or 2-hydroxypropyl; or a (C 1-4 )alkoxy(C 1-4 )alkyl group such as methoxyethyl, ethoxyethyl or methoxypropyl, a C 3 to C 12 cycloalkyl group such as an isobornyl group, a C 3 to C 20 aryl group such as a phenyl group, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched C 1-4 alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group, R 3 may also be a group —(C 2 H 4 O) m —R″, with m=5 to 150 and R″═H or C 1 to C 30 alkyl, for example —POE-methyl or —POE-behenyl; (iii) the (meth)acrylamides of formula: in which R 8 denotes H or methyl; and R 7 and R 6 , which may be identical or different, represent: a hydrogen atom; or a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; R 3 may especially be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyclohexyl, t-butyl-cyclohexyl or stearyl group; 2-ethylperfluorohexyl; or a C 1-4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl or 2-hydroxypropyl; or a (C 1-4 )alkoxy(C 1-4 )alkyl group such as methoxyethyl, ethoxyethyl or methoxypropyl, a C 3 to C 12 cycloalkyl group, such as an isobornyl group, a C 3 to C 20 aryl group such as a phenyl group, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched C 1 -C 4 alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group, or a phenyl group; (iv) the vinyl compounds of formulae: CH 2 ═CH—R 9 , CH 2 ═CH—CH 2 —R 9 or CH 2 ═C(CH 3 )—CH 2 —R 9 in which R 9 is a hydroxyl group, halogen (Cl or F), NH 2 , OR 10 in which R 10 represents a phenyl group or a C 1 to C 12 alkyl group (the monomer is a vinyl or allylic ether); acetamide(NHCOCH 3 ); a group OCOR 11 in which R 11 represents a linear or branched alkyl group of 2 to 12 carbons (the monomer is a vinyl or allylic ester); or a group chosen from: a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; a C 3 to C 12 cycloalkyl group such as isobornyl or cyclohexane, a C 3 to C 20 aryl group such as phenyl, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl; benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched 1 to 4 C alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si(R 4 R 5 ) in which R 1 and R 2 , which may be identical or different, represent a C 1 to C 6 alkyl group, or a phenyl group; (v) (meth)acrylic, (meth)acrylamide or vinyl monomers containing a fluoro or perfluoro group, such as ethylperfluorooctyl or 2-ethylperfluorohexyl (meth)acrylate; (vi) silicone-based (meth)acrylic, (meth)acrylamide or vinyl monomers, such as methacryloxypropyltris(trimethylsiloxy)silane or acryloxypropylpolydimethylsiloxane; (vii) ethylenically unsaturated monomers comprising at least one carboxylic, phosphoric or sulfonic acid, or anhydride, function, for instance acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, acrylamidopropanesulfonic acid, vinylbenzoic acid and vinylphosphoric acid, and the salts thereof; (viii) ethylenically unsaturated monomers comprising at least one tertiary amine function, for instance 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate or dimethylaminopropylmethacrylamide, and the salts thereof.
19 . The composition as claimed in one of claims 15 to 18 , in which the additional comonomer(s) is (are) present in an amount of from 30% to 99.99% by weight, especially in an amount of from 50% to 99.9% by weight, in particular from 70% to 99.5% by weight, or even from 80% to 99% by weight, and better still from 90% to 98% by weight, relative to the weight of the final polymer.
20 . The composition as claimed in one of claims 15 to 19 , in which the additional comonomers are chosen, alone or as a mixture, from C 1 -C 18 alkyl or C 3 -C 12 cycloalkyl(meth)acrylates, and especially from methyl acrylate, methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, trifluoroethyl acrylate and trifluoroethyl methacrylate; or alternatively acrylic acid, methacrylic acid, methacryloxypropyltris(trimethylsiloxy)silane, acryl-oxypropyltris(trimethylsiloxy)silane, acryloxypropyl-polydimethylsiloxane and methacryloxypropylpoly-dimethylsiloxane.
21 . The composition as claimed in one of claims 15 to 20 , in which the polymer has a weight-average molecular mass (Mw) of between 5000 and 600 000 g/mol, especially between 10 000 and 300 000 g/mol and better still between 20 000 and 150 000 g/mol.
22 . The composition as claimed in one of the preceding claims, in which the polymer is present, alone or as a mixture, in an amount of from 0.01% to 60% by weight, preferably 0.1% to 50% by weight, especially 1% to 25% by weight or even 3% to 15% by weight and better still 5% to 12% by weight, relative to the total weight of the composition.
23 . The composition as claimed in one of the preceding claims, in which the physiologically acceptable medium comprises a hydrophilic medium comprising water or a water/hydrophilic organic solvent(s) mixture and/or comprises a fatty phase.
24 . The composition as claimed in one of the preceding claims, in which the fatty phase comprises waxes, pasty fatty substances, gums, lipophilic organic solvents and oils, and/or mixtures thereof.
25 . The composition as claimed in one of the preceding claims, also comprising a particulate phase that may comprise pigments and/or nacres and/or fillers.
26 . The composition as claimed in one of the preceding claims, comprising dyestuffs chosen from water-soluble dyes and/or liposoluble dyes.
27 . The composition as claimed in one of the preceding claims, comprising at least one additional polymer such as a film-forming polymer.
28 . The composition as claimed in one of the preceding claims, comprising at least one ingredient chosen from vitamins, thickeners, gelling agents, trace elements, softeners, sequestrants, fragrances, acidifying or basifying agents, preserving agents, sunscreens, surfactants, antioxidants, hair-loss counteractants, antidandruff agents, propellants and ceramides, or mixtures thereof.
29 . The composition as claimed in one of the preceding claims, which is in the form of a suspension, a dispersion especially of oil in water by means of vesicles; an optionally thickened or even gelled oily solution; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; an oily or emulsified gel;
a dispersion of vesicles, especially lipid vesicles; a two-phase or multi-phase lotion; a spray; a loose, compact or cast powder; an anhydrous pastep; a lotion, a cream, a pomade, a soft pastep, an ointment, a cast or molded solid especially as a stick or in a dish, or alternatively a compacted solid.
30 . The composition as claimed in one of the preceding claims, which is in the form of a care and/or makeup product for bodily or facial skin, the lips, the nails, the eyelashes, the eyebrows and/or the hair, an antisun or self-tanning product, or a hair product for caring for, treating, shaping, making up or dyeing the hair.
31 . The composition as claimed in one of the preceding claims, which is in the form of a makeup composition, especially a complexion product such as a foundation, a makeup rouge or an eyeshadow; a lip product such as a lipstick or a lipcare product; a concealer product; a blusher, a mascara or an eyeliner; an eyebrow makeup product, a lip pencil or an eye pencil; a nail product such as a nail varnish or a nailcare product; a body makeup product; a hair makeup product (hair mascara or hair lacquer); a composition for protecting or caring for the skin of the face, the neck, the hands or the body, especially an antiwrinkle composition or a moisturizing or treating composition; an antisun or artificial tanning composition; a hair product, especially for dyeing, holding the hairstyle, shaping the hair, caring for, treating or cleansing the hair, such as shampoos, hairsetting gels or lotions, blow-drying lotions, and fixing and styling compositions such as lacquers or sprays.
32 . A cosmetic process for making up or caring for keratin materials, especially bodily or facial skin, the lips, the nails, the eyelashes, the eyebrows and/or the hair, comprising the application to said materials of a cosmetic composition as defined in any one of claims 1 to 31 .
33 . A monomeric compound of formula (I):
in which:
R1 represents a linear, branched and/or cyclic, saturated and/or unsaturated carbon-based radical, preferably alkyl, containing 2 to 22 carbon atoms and especially 8 to 16 carbon atoms; optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
R 2 and R 3 , present on the same ring or each on a different ring, represent, independently of each other, a hydrogen, a halogen or a group of formula —X-G-P (II), with the proviso that at least one of the radicals R 2 and/or R 3 represents a group of formula (II), in which:
X is chosen from —O—, —S—, —SO—, —SO 2 —, —NH— and —NR 4 — groups with R 4 representing a linear, branched and/or cyclic, saturated and/or unsaturated carbon-based radical containing 2 to 30 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
G is a linear, branched and/or cyclic, saturated and/or unsaturated divalent carbon-based radical, containing 2 to 32 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S;
P is a polymerizable group chosen from one of the following formulae:
in which:
R′ represents H or a linear or branched, saturated C 1-6 hydrocarbon-based radical,
X′ represents O, NH or NR″ with R″ representing a radical chosen from C 1-6 alkyl, C 6-10 aryl, (C 6-10 )-aryl(C 1-6 )alkyl and (C 1-6 )alkyl(C 6-10 )aryl radicals, the alkyl and/or aryl groups also possibly being substituted with one or more groups chosen from OH, halogen, C 1-6 alkoxy and C 6-10 aryloxy;
m is equal to 0 or 1;
n is equal to 0 or 1;
p is equal to 0, 1 or 2,
with the exclusion of the compounds of formula (I) for which, simultaneously, R 2 is H, X is NH, P is of formula (IIIa), m=1, R′ is H or CH 3 , X′ is O or NR″ and R1 is a C 1 -C 6 alkyl radical, a C 6 -C 10 aryl radical, a (C 6 -C 10 )aryl(C 1 -C 6 )alkyl radical or a (C 1 -C 6 )alkyl(C 6 -C 10 )aryl radical, said alkyl and/or aryl radicals being optionally substituted with a hydroxyl, a halogen, a (C 1 -C 6 )alkoxy or a (C 6 -C 10 )aryloxy.
34 . The monomeric compound as claimed in claim 33 , in which R1 is a cyclic, linear and/or branched, saturated or unsaturated hydrocarbon-based radical, optionally comprising a hydrocarbon-based ring which is itself saturated or unsaturated, containing 3 to 18 and especially 8 to 16 carbon atoms, and may comprise at least one heteroatom, especially one or two nitrogen, oxygen or silicon atoms.
35 . The monomeric compound as claimed in either of claims 33 and 34 , in which R1 is a linear, branched and/or cyclic, saturated or unsaturated hydrocarbon-based radical containing 8 to 16 carbon atoms.
36 . The monomeric compound as claimed in claim 33 , in which R1 is chosen from n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, cyclooctyl, decyl, cyclodecyl, dodecyl, cyclododecyl, p-tert-butylcyclohexyl, benzyl and phenyl radicals or a radical chosen from ethyl-2-N-pyrrolidine, (2-methyl)-1-ethylpyrrolidine, 3-propyltriethoxysilane, dialkylpyrimidines and especially 2-(4,6-dimethyl)pyrimidine, the benzothiazyl radical and the fluorenyl radical.
37 . The monomeric compound as claimed in one of claims 33 to 36 , in which the radical R 2 is a hydrogen atom and R 3 is a group of formula (II).
38 . The monomeric compound as claimed in one of claims 33 to 37 , in which, in said group of formula (II), X is chosen from —O—, —S—, —NH— and —NR 4 —.
39 . The monomeric compound as claimed in one of claims 33 to 38 , in which the radical R 4 represents a linear, branched and/or cyclic, saturated or unsaturated hydrocarbon-based radical optionally comprising a hydrocarbon-based ring that is itself saturated or unsaturated, containing 2 to 18 and especially 3 to 12 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P, Si and S; especially an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, octyl, decyl, dodecyl, phenyl or benzyl radical.
40 . The monomeric compound as claimed in one of claims 33 to 39 , in which the divalent radical G is a linear, branched and/or cyclic, saturated or unsaturated divalent hydrocarbon-based radical optionally comprising a hydrocarbon-based ring that is itself saturated or unsaturated, containing in total 2 to 18 and especially 3 to 10 carbon atoms, optionally substituted with one or more groups chosen from ═O, OH, NH 2 and halogen atoms; and/or optionally interrupted with one or more heteroatoms chosen from O, N, P and Si.
41 . The monomeric compound as claimed in one of claims 33 to 40 , in which G is chosen from linear or branched, saturated divalent hydrocarbon-based radicals optionally comprising a saturated hydrocarbon-based ring, containing in total 2 to 18 and especially 3 to 10 carbon atoms.
42 . The monomeric compound as claimed in one of claims 33 to 41 , in which G is chosen from ethylene, n-propylene, isopropylene (or 1-methylethylene and 2-methylethylene), n-butylene, isobutylene, pentylene, especially n-pentylene, hexylene, especially n-hexylene, heptylene, cyclohexylene, octylene, decylene, cyclohexyldimethylene especially of formula —CH 2 —C 6 H 10 —CH 2 —, and dodecylene radicals.
43 . The monomeric compound as claimed in one of claims 33 to 42 , in which the polymerizable group P is chosen from one of the following formulae:
in which R′ represents H or methyl.
44 . The monomeric compound as claimed in one of claims 33 to 43 , corresponding to one of the following formulae:
45 . A polymer comprising at least one monomeric compound as defined in one of claims 33 to 44 .
46 . The polymer as claimed in claim 45 , characterized in that it is a homopolymer of a monomeric compound as defined in one of claims 33 to 44 .
47 . The polymer as claimed in claim 45 , characterized in that it is a copolymer comprising only monomeric compounds as defined in one of claims 33 to 44 .
48 . The polymer as claimed in claim 47 , characterized in that the monomeric compounds are each present in a proportion of from 0.5% to 99.5% by weight, especially 5% to 95% by weight, or even 10% to 90% by weight and better still each in a proportion of from 30% to 70% by weight, relative to the total weight of the polymer.
49 . The polymer as claimed in claim 45 , characterized in that it is a copolymer comprising at least one monomeric compound as defined in one of claims 1 to 12 , and at least one additional comonomer.
50 . The polymer as claimed in claim 45 , characterized in that it is a statistical, alternating, grafted, block or gradient copolymer.
51 . The polymer as claimed in either of claims 49 and 50 , characterized in that the monomeric compound is present in an amount of from 0.01% to 70% by weight relative to the weight of said polymer, especially in an amount of from 0.1% to 50% by weight, in particular from 0.5% to 30% by weight, or even from 1% to 20% by weight and better still from 2% to 10% by weight, the additional comonomers, alone or as a mixture, representing the remainder to 100% by weight.
52 . The polymer as claimed in one of claims 49 to 51 , characterized in that it comprises at least one additional hydrophilic comonomer, or a mixture of such comonomers, which may be present in a proportion of from 1% to 99.99% by weight, especially 2-70% by weight, better still 5-50% by weight or even 10-30% by weight, relative to the total weight of the copolymer.
53 . The polymer as claimed in one of claims 49 to 51 , characterized in that it comprises at least one additional hydrophobic comonomer, or a mixture of such comonomers, which may be present in a proportion of from 1% to 99.99% by weight, especially 30-98% by weight, better still 50-95% by weight or even 70-90% by weight, relative to the total weight of the copolymer.
54 . The polymer as claimed in one of claims 49 to 51 , characterized in that it comprises at least one additional comonomer chosen, alone or as a mixture, from the following monomers:
(i) ethylenic hydrocarbons containing from 2 to 10 carbons, such as ethylene, isoprene or butadiene; (ii) the (meth)acrylates of formula: CH 2 ═CHCOOR 3 or in which R 3 represents: a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; R 3 may especially be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyclohexyl, t-butyl-cyclohexyl or stearyl group; 2-ethylperfluorohexyl; or a C 1-4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl or 2-hydroxypropyl; or a (C 1-4 )alkoxy(C 1-4 )alkyl group such as methoxyethyl, ethoxyethyl or methoxypropyl, a C 3 to C 12 cycloalkyl group such as an isobornyl group, a C 3 to C 20 aryl group such as a phenyl group, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched C 1-4 alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si (R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group, R 3 may also be a group —(C 2 H 4 O) m —R″, with m=5 to 150 and R″═H or C 1 to C 30 alkyl, for example —POE-methyl or —POE-behenyl; (iii) the (meth)acrylamides of formula: in which R 8 denotes H or methyl; and R 7 and R 6 , which may be identical or different, represent: a hydrogen atom; or a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and groups Si (R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; R 3 may especially be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyclohexyl, t-butyl-cyclohexyl or stearyl group; 2-ethylperfluorohexyl; or a C 1-4 hydroxyalkyl group such as 2-hydroxyethyl, 2-hydroxybutyl or 2-hydroxypropyl; or a (C 1-4 )alkoxy(C 1-4 )alkyl group such as methoxyethyl, ethoxyethyl or methoxypropyl, a C 3 to C 12 cycloalkyl group, such as an isobornyl group, a C 3 to C 20 aryl group such as a phenyl group, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched C 1 -C 4 alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si (R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group, or a phenyl group; (iv) the vinyl compounds of formulae: CH 2 ═CH—R 9 , CH 2 ═CH—CH 2 —R 9 or CH 2 ═C(CH 3 )—CH 2 —R 9 in which R 9 is a hydroxyl group, halogen (Cl or F), NH 2 , OR 10 in which R 10 represents a phenyl group or a C 1 to C 12 alkyl group (the monomer is a vinyl or allylic ether); acetamide(NHCOCH 3 ); a group OCOR 11 in which R 11 represents a linear or branched alkyl group of 2 to 12 carbons (the monomer is a vinyl or allylic ester); or a group chosen from: a linear or branched alkyl group of 1 to 18 carbon atoms, in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si(R 4 R 5 ), in which R 4 and R 5 , which may be identical or different, represent a C 1 to C 6 alkyl group or a phenyl group; a C 3 to C 12 cycloalkyl group such as isobornyl or cyclohexane, a C 3 to C 20 aryl group such as phenyl, a C 4 to C 30 aralkyl group (C 1 to C 8 alkyl group) such as 2-phenylethyl; benzyl, a 4- to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N and S, the ring being aromatic or non-aromatic, a heterocycloalkyl group (1 to 4 C alkyl), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms and linear or branched 1 to 4 C alkyl groups in which is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups also possibly being optionally substituted with one or more substitutents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F) and groups Si(R 4 R 5 ) in which R 1 and R 2 , which may be identical or different, represent a C 1 to C 6 alkyl group, or a phenyl group; (v) (meth)acrylic, (meth)acrylamide or vinyl monomers containing a fluoro or perfluoro group, such as ethylperfluorooctyl or 2-ethylperfluorohexyl (meth) acrylate; (vi) silicone-based (meth)acrylic, (meth)acrylamide or vinyl monomers, such as methacryloxypropyltris(trimethylsiloxy)silane or acryloxypropylpolydimethylsiloxane; (vii) ethylenically unsaturated monomers comprising at least one carboxylic, phosphoric or sulfonic acid, or anhydride, function, for instance acrylic acid, methacrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, maleic acid, acrylamidopropanesulfonic acid, vinylbenzoic acid and vinylphosphoric acid, and the salts thereof; (viii) ethylenically unsaturated monomers comprising at least one tertiary amine function, for instance 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate or dimethylaminopropylmethacrylamide, and the salts thereof.
55 . The polymer as claimed in claim 54 , characterized in that the additional comonomer(s) is (are) present in an amount of from 30% to 99.99% by weight, especially in an amount of from 50% to 99.9% by weight, in particular from 70% to 99.5% by weight or even from 80% to 99% by weight and better still from 90% to 98% by weight relative to the weight of the final polymer.
56 . The polymer as claimed in one of claims 49 - 51 and 54 - 55 , characterized in that the additional comonomers are chosen, alone or as a mixture, from C 1 -C 18 alkyl or C 3 -C 12 cycloalkyl(meth)acrylates, and especially from methyl acrylate, methyl methacrylate, isobornyl acrylate, isobornyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, trifluoroethyl acrylate and trifluoroethyl methacrylate; or alternatively acrylic acid, methacrylic acid, methacryloxypropyltris(trimethyl-siloxy)silane, acryloxypropyltris(trimethylsiloxy)-silane, acryloxypropylpolydimethylsiloxane and methacryloxypropylpolydimethylsiloxane.
57 . The polymer as claimed in one of claims 49 to 56 , characterized in that it has a weight-average molecular mass (Mw) of between 5000 and 600 000 g/mol, especially between 10 000 and 300 000 g/mol and better still between 20 000 and 150 000 g/mol.
58 . The use of at least one monomeric compound as defined in one of claims 33 to 44 , or of at least one polymer as defined in one of claims 45 to 57 , in a composition, for giving said composition optical effects, especially fluorescence or optical-brightening effects.Join the waitlist — get patent alerts
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